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Synthesis of alkyl glycosides from cyclodextrin using cyclodextrin glycosyltransferase from Paenibacillus sp. RB01

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Abstract

Alkyl glycosides have potential use as biodegradable detergents due to their high surface activity with low toxicity. Recent progress in the application of enzymes to the preparation of these surface-active compounds demonstrates the advantages to the chemical synthesis. In this work, alkyl glycosides were, for the first time, synthesized from cyclodextrin (CD) and various soluble alcohols by transglycosylation reaction using cyclodextrin glycosyltransferase (CGTase) from Paenibacillus sp. RB01. Several alcohols (methanol, ethanol, 1-propanol, 2-propanol, 1-butanol and 2-butanol) as glycosyl-acceptor substrates were evaluated. It was found that the reaction products which were analyzed by TLC were maximum for 30% methanol, 20–30% ethanol, 10–20% 1-propanol, 10% 2-propanol, 8% 1-butanol and 5–10% 2-butanol. In addition, the increase in the yield of alkyl glycoside formation was achieved by using methanol as an acceptor. Optimal reaction conditions for methyl glycoside synthesis from CD were to incubate 1.2% (w/v) β-CD and 240 U/mL of CGTase in a water/methanol system containing 30% (v/v) methanol, pH 6.0 and a temperature of 40 °C. At least three main methyl glycoside products were formed having 1–3 monosaccharide units attached to methanol which were in accordance with the results of MS analysis.

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Acknowledgments

This research was supported by Ratchadapiseksompote Research Fund granted to Starch and Cyclodextrin Research Unit, Department of Biochemistry, Faculty of Science, Chulalongkorn University. The support from the Thai Government Stimulus Package 2 (TKK2555) under the project PERFECTA is also acknowledged.

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Authors and Affiliations

  1. Starch and Cyclodextrin Research Unit, Department of Biochemistry, Faculty of Science, Chulalongkorn University, Bangkok, 10330, Thailand

    Kwanjai Chotipanang & Manchumas Hengsakul Prousoontorn

  2. Organic Synthesis Research Unit, Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok, 10330, Thailand

    Worawan Bhunthumnavin

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  1. Kwanjai Chotipanang
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  2. Worawan Bhunthumnavin
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  3. Manchumas Hengsakul Prousoontorn
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Correspondence to Manchumas Hengsakul Prousoontorn.

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Chotipanang, K., Bhunthumnavin, W. & Prousoontorn, M.H. Synthesis of alkyl glycosides from cyclodextrin using cyclodextrin glycosyltransferase from Paenibacillus sp. RB01. J Incl Phenom Macrocycl Chem 70, 359–368 (2011). https://doi.org/10.1007/s10847-010-9888-z

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